


Derek: Whore no More

by Always_Bottom_Derek



Category: Teen Wolf (TV)
Genre: Anal Sex, Blow Jobs, Bottom Derek Hale, Closet Chubby Chaser Derek, Daddy Kink, Homophobic Language, M/M, Not safe for work pic at the start, Prostitution, Reader-Insert, Rough Kissing, submissive Derek Hale
Language: English
Status: Completed
Published: 2018-09-07
Updated: 2018-09-07
Packaged: 2019-07-08 00:26:25
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,163
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15919257
Author URL: https://archiveofourown.org/users/Always_Bottom_Derek/pseuds/Always_Bottom_Derek
Summary: So, rentboy Derek.He became a rent boy because he needs the money. There was no huge insurance settlement after the fire, here. There was nothing left at all.Not that you care. Whatever his story is, you think he must be earning some good cash now. Especially if the pics on his profile are anything to go by, him in his painted on jeans, accentuating his fat ass.It's fun to fantasize, looking at Derek's pictures. But you want more than fantasy. You want the real thing.And tonight you're going to get it.





	Derek: Whore no More

 

                                                                        

Reader inserts (Ha! “inserts”) aren’t normally my thing but here it goes…

* * *

 

So, rentboy Derek.

Derek became a rent boy because he needed the money. There was no huge insurance settlement after the fire, here. There was nothing left at all.

Not that you care. Whatever his story is, you think he must be earning some good cash now. Especially if the pics on his profile are anything to go by, him in his painted on jeans, accentuating his fat ass. In your favorite one, the pair he wears is ripped at the base of his buttcheeks so their plump curves hang out through the tears.

Looking at that pic, you think it’d be hot to fuck him while he was still wearing those jeans. Maybe you'd just rip open a hole in the back of ‘em for access. Or widen one of the tears that are already there.

Exposing more of those muscular cheeks, you imagine he’s bare ass naked underneath. Or maybe just wearing a jock. You picture him, his naked ass cheeks pressing back into you because he wants your dick in his hungry hole.

The fantasy is fun, but you want more than that.

So, you send an inquiry. Derek responds and the two of you schedule an “appointment.” His services aren’t cheap, but he’s not that expensive either. Not that it would’ve mattered if he was spendy; you have plenty enough money to pay for his time and his body.

Derek comes to your house. He shows up on time dressed like a total slut in, as you requested, the torn jeans in your favorite pic.

Under this should be your second request: a jockstrap like you saw in your fantasy. Up top, he has on a white tank and a black leather jacket, also as you directed.

It’s good to see he can follow orders.

When you greet him you’re surprised. In reality, Derek is far from the defiant, scowling alpha that stared out at you from his profile pics.

He certainly doesn’t seem confident now. It’s funny, meeting in person he acts embarrassed about what he does. He’s a little quiet, sweetly shy. Every now and then a hesitant smile slips out. (He has these cute big teeth.)

Maybe it’s your mansion, maybe it’s you, he clearly seems a little awed. While there’s something attractive in his unsurety, you hope this doesn’t impact his job performance.

Still, you’re kind to him in your intros, treat him like an actual human, and this seems to throw him off balance.

If you could read his mind you’d quickly know already you’ve been more considerate than most of his usual clients. The guys he’s met hooking have been real assholes overall.

Plus, in his secret heart, Derek’s always had a thing for fat dudes and you check that box for sure. You don’t know it yet but this combination incites him to make this “session” good for you.

After some casual chat and sparkling water (since Derek doesn’t “drink on the job”), you lead him from the entry lounge up to your chambers. He follows you into the bedroom, his jacket already sliding down off his shoulders revealing those fantastic arms of his.

When you get inside, he closes the door behind the two of you. His jacket drops to the floor and he steps up close enough you can smell all the subtleties of him. He asks in a low, breathy voice what’s next? Offers, after a moment of silence, if maybe you want to touch him?

You do. Definitely.

He stands perfectly still, giving you access to his body. You run your hands over his bare arms, across the cotton ribbing covering his rock hard abs.

Derek lifts the hem of his shirt up so you can access more skin. He sighs as your fingers trace the ridges of his marvelous stomach because even though he fucks for a living he’s touch-starved.

And the way you touch him turns him on: kind and tentative even though you’ve bought him.

It does something to him how your expression is intent and admiring but that you’re also checking in with him with quick flickering glances.

Then your gazes lock.

It’s Derek who breaks the silence, whispering, “I want more.” In his next breath, he asks you if you would take his shirt off all the way. Watches you, eyes moving between your hands and your face as you grab the bottom of his shirt and slide it.

You lift it up and when he bows his head (this small submission looks amazing on him) for you to pull it off, instead you just hook the front over the back of his neck, putting him in a wife-beater yoke. His head pops up, kind of shocked at this move but he settles quickly when your big hands soothe over his full, hard pecs.

You see the way his eyes flutter when you graze his nipples, so you start paying them some real attention. He can’t stop from moaning like a bitch at your touch. There’s no acting here, you can tell. The sound is pure.

You pinch his nipples. Twist them between your thick fingers. Derek pushes into this rougher touch. His breath gets heavy.

You see the front of his jeans tighten. You know from the pics of him posted online he’s got a huge, fat cock. What you don’t know is that he’s never gotten it up this easy for a customer. In fact, a lot of times when guys fuck him, he never gets hard at all.

You’re surprised when he leans in. It’s clear he’s silently petitioning you for a kiss. You have a good four inches on him, so you easily reach over and cup that thick, powerful neck of his. His eyes drift closed, loving your gentle manhandling.

He’s used to being the one leading and it feels so good to let you take control here. Your thumbs hook just behind his ears as you pull him in closer and close the distance.

His lips open, mouth parting, inviting you in. You kiss him. Soft. Just for a moment. But when he whines into your mouth, that opens the floodgates.

You kiss him hard then, deep and dirty. Savoring his skilled tongue, you plunder his mouth. When you part, your spit shining on his lips, “Can I suck your cock?” are the first words he utters.

His voice is hesitant because more often than you’d guess, it’s his Johns who are wanting a mouthful of his lush dick.

His hand follows his voice, underlining his want. He reaches it out his and slides it down the front of you. Rubbing over your big soft belly on his way to your crotch, he grabs your cock through your jeans.

You’re no slouch in the dick department either. Derek’s eyes get wide when he feels just how big you are. Tongue darting out, he licks his still kiss-slick lips.

Most of his clients are average at best and the feel of your massive meat excites him.

Without waiting for you to even answer him, he drops to his knees and fumbles with your buckle, too eager to see what you’re packing. Nuzzling into the fabric he opens your fly, already mouthing at the outline of your dick through the denim, wanting to taste you before he even has your pants open.

You grab a fist full of his hair to keep him from diving in too quickly. Tell him to start slow as he pulls your briefs down to reveal his prize.

You feel his hot breath on you and savor it when the wet heat of his mouth slides over your cockhead for the first time.

He sucks your tip. Plays with your foreskin, dipping his tongue under it, teasing you to even greater hardness, sucking that sheath of skin over the head of your dick.

You tighten the fingers in his bangs. Derek doesn’t stop what he’s doing, just he looks up at you. Over your big belly it's almost hard to see those large expressive eyes of his measuring your every reaction.

He _really_ wants to make this good for you.

Moving backward, your hand remains in his hair. Keeping your dick in his mouth he follows you on his knees. You reach the edge of the bed where you settle down, Derek’s dark head between your spread thighs.

You watch as he slides deeper over your cock trying to fit all of you in his mouth, down his throat. You’re so big, so thick…

His mouth stretches wide taking you in.

Derek hasn’t felt his gag reflex in years, but you’re so long. He chokes on your dick but he’s determined to swallow all of it down. He wants to prove himself worthy of such magnificence.

When his throat spasms, you stop him. Make him back off. You’re concerned. But this just makes him want to please you even more.

So he offers you his ass.

Standing up, he turns around, giving you a view of the rips in the seat of his jeans. They look so much better in person, his round asscheeks hanging down.

It’s your fantasy come to life.

Derek roughly whispers for you to fuck him. His voice is broken with his beg: he wants it bare, your cock in his tight ass-pussy. He promises over and over he’s clean. Swears he always uses condoms and never gets fucked without them on a job.

Well, until now.

He steps back, all but shoving his ass in your face. You stroke a fuzzy cheek through the rent in his jeans while he begs you to tear into him. The shred of fabric fills the room as you rip the back of those jeans wide open, revealing Derek’s full, meaty ass.

Wearing his jeans now like assless chaps, Derek reaches around and pulls his cheeks apart showing you his hole.

It’s hairless, dusky and perfect. Not at all as used-looking you expected. But then Derek does get hired to top an awful lot.

It could be one of the most beautiful moments of your life, seeing that ass and knowing for the next few hours it belongs to you and you alone. The most beautiful moment, however, follows quickly after when he asks you to spit on that pristine star and open him up.

That blowjob he gave you has made him crave your cock in his ass. Badly. So, the second your finger traces that perfect pucker he presses back onto it.

Derek is in such a hurry to get any part of you into him.

Your finger slides in and he’s so fucking tight around you. His insides so smooth and warm. Surprisingly wet. Almost like a real bitch would be.

He begs loudly for your cock now, even though he’s still so tight around your finger. You’re worried about hurting him and say so, but this just makes him hotter. The next thing you know he’s got your cock in his hand and is feeding it into his asshole.

You watch his whore pussy stretch wide to accommodate you. Feel how that tight rim breaks for you, letting you in.

It’s so much better than you could have even imagined… No fantasy could have ever prepared you for how fucking exquisite it feels: that moment when your fat cockhead finally breaches him and slips in past his rim.

So tight around your tip. Hot, slick, soft.

Derek whines in pain but no sooner is the tip of your cock in him than he starts rocking back and forth. Groaning and grunting because you’re fucking stretching him to his limit.

You know you should tell him to ease off but it feels soooo good. Him working that fat bubble ass of his. Fucking your cock into him.

Derek moans in between ragged pants about how big you are. How good it hurts. How much he loves the feel of your big dick in his ass.

He doesn’t stop pulsing his hips until he’s backed himself up on your cock so you’re in balls deep.

God… the heat of his ass around you. The wet silk of his mancunt is amazing.

His anal muscles clench, his body is still not quite sure if it wants to push your invading length out or suck you in deeper. Despite his profession, he’s so fucking tight. It’s almost uncomfortable.

Almost.

It makes you wonder if you’re ever gonna be able to get out of him. Alhough there’s a perverse appeal in the thought of being forever sheathed in Derek’s glorious man-pussy.

Then he starts moving again.

He slides up and down your dick. Releasing and squeezing you in the most fantastic way. Stopping just before the head of your cock is about to pop out and then riding backward.

In the same way you’d love to live in his hole, by the time he’s so thoroughly fucked himself on your cock, he’s never gonna let you rest. You’ll have wrecked him. He’s going to want you stretching his fine, fat ass constantly.

But you can worry about that later, because right now you’re in love with watching the round globes of his ass jiggle as he bounces up and down once he gets his rhythm.

Fuck yeah, this is what you’d hoped for when you bought him: just to get to lay back and watch him go to town. And Derek is practically twerking on your dick.

Moaning like a bitch in heat, he fucks himself like that, with his back to you initially. But then he pulls off just long enough to push you onto your back on the bed. He kicks out of his cowboy boots and shucks off his ruined jeans so that he’s left only in his jock and a pair of clean white socks.

He crawls up on the bed, kissing his way up your body, nuzzling worshipfully at your big belly and hairy man tits before he sits on your cock. Facing you, now you get to watch that pretty mug of his. All those slutty expressions of rapture as he impales himself on your dick.

His green eyes are filled with heat and shame as he asks you to call him a “slut.”

And how can you deny him when he asks so prettily? Your dirty whore/rentboy. So you call him a slut and more. Faggot. Whore. Cumdump. Cockslut.

His face reddens but his hard dick is spurting little gluts of precum inside the cup of his jock as it bounces against your belly. High on your cock and the potent cocktail of humiliation, Derek’s tongue is loosed and he begins confessing even as he’s working your dick.

How he wants you to make him your bitch. Wants you to own his ass. Not that he thinks he deserves you. But he wants to be worthy.

He tells you how he needs the money he gets from fucking and being fucked, but that if he’d had a cock like yours, he would have quit long ago. He tells you he would give his whoring up right now if it meant starving so he could service you for the rest of his days.

You just feel so damn good inside him.

Derek promises that if you’ll accept him you can have his ass whenever you want it. For free. That even if you don’t, from here on out he’ll cancel any appointment for the chance to spend some time with you.

He says all these things as he’s grinding down on your dick. Riding you. Sliding his ass back and forth. His thick thighs flexing.

Your hands grip at his hips. They shift occasionally to run over his smooth muscles. In response, he bends down to press intermittent kisses and suckle your big pecs.

Plush lips and a warm, wet, mouth suckle on your nipples, while that hot, tight ass works your cock.

By now he’s lost some of his fervor. His riding has become indulgent and lazy, his kisses languid. At least until you startle him with a few rough thrusts of your prick.

Derek groans and the word “daddy” just slips out.

His face gets all red when he realizes what he said. But you like it: the title and the embarrassed little boy look on his stubbled alpha face. The contrast is delicious.

So you spank him and tell him to say it again. His ass grips your cock with each “smack!” You don’t let up until he’s crying a little. His asscheeks redder than those of his face.

Derek loves this though. His rhythm picks up again and soon he’s growling and gasping, “I need your cum, Daddy.

“You feel so fucking good in my ass.”

“Breed your bitch, please, Daddy.”

“Daddy…”

“Daddy…”

“I need…”

The pouch of his jock is dark, soaked with pre-cum. He’s not even touching himself but it’s clear he’s all but cumming.

He’s so entranced by your thick, long rod inside him he’s barely even thought about his own dick. If it wasn’t for the jock, his neglected cock would be slapping against his low belly, bouncing as hard as his ass is.

But he doesn’t even think of pulling it out and stroking himself, all he’s thought about is the way you’re rubbing him just right. Your fat daddy dick presses his prostate so hard you’re practically milking him.

But even in this, he’s determined his pleasure comes second to yours. So he doubles down. More than anything he’s focused on making this fuck the best of your life.

And this, Derek lost in pleasing you, is a glorious vision for you to cum to.

His ripped body atop you. That ass around your cock. Him staring deep into your eyes. His wrecked voice begging you to breed him.

“Fucking breed me, make my ass yours.

“Fill me up, Daddy.

“Own this slutty ass. Make me come for you…”

Quiet as he seemed when you first met him, Derek’s lust is at a boil and his words bubble up and spill out just like the spunk rising from your balls.

“I need your seed.

“I want you dripping out of me for days.

“Own me… Mark me up… Show everyone else I belong to you.

“I want to belong to you.

“Everyday.

“My ass, my mouth…

“Everything.

“Let me be your fucktoy.

“Your bitch boy.

“Your personal whore.

”Please….”

After reciting this profane poetry, Derek leans lean up and kisses you hard. His ass pulses around your cock. His tongue begs you to make a claim.

You answer by flipping the both of you over, your movements fast despite you bulk. You pin him under you. Roaring atop him as he writhes and whines you brand his insides with your hot heavy load.

In that moment both of you know Derek’s whoring days are over.

**Author's Note:**

> Thanks for reading. I have started posting shorter works like these on tumblr. under Always Bottom Derek. I make no promises but this seems to be getting me back into writing (at the moment). So let's all enjoy it while it lasts.
> 
> Thanks for the read.


End file.
